Organic Letters
Organic Letters
5 years ago

Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide

Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide
Sagiri Watanabe, Maki Yokoyama, Kazuto Takaishi, Sota Sasaki, Hiromi Ota, Tadashi Ema
Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of epoxides. A catalytic cycle proposed was supported by DFT calculations.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01838

DOI: 10.1021/acs.orglett.7b01838

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